Anything that's a must-own he will have, but some of them will be old and need replacing soon and he'll also have a long list of things he'd like to have, but can't justify because he's saving for the esential stuff that will need replacing next year.

We can't tell you what is on either list (unless it's something comsumable, like rum or chocolate) but you would find out pretty quickly if you go for a sail with him. Sailors like talking about their boat and all the work they've done.